Herbicidal compositions

ABSTRACT

New compounds corresponding to the generic formula:   wherein X can be oxygen or sulfur, R can be lower alkyl or two R groups can form a ring structure, R1 can be hydrogen, halogen, haloalkyl, alkyl or alkoxy.

United States Patent [1 1 11] 3,917,647 Mihailovski Nov. 4, 1975 HERBICIDAL COMPOSITIONS Primary ExaminerDonald Gi. Daus Assistant EmminerMark L. Berch 7 l 51 Inventor 25:33:" Mlhallovskl Berke Attorney, Agent, or FirmDaniel C. Block [73] Assignee: Stauffer Chemical Company,

Westport, Conn. [57] ABSTRACT [22] Filed Jan 4 1974 New compounds corresponding to the generic formula: [21] Appl. No.: 430,809

Related US. Application Data R H [60] Continuation-impart of Ser. No. 247,670, April 26, 2

1972, abandoned, which is a division of SCI. No. R R 99,658, Dec. 18, 1970, abandoned.

[52] US. Cl. 260/326.25; 260/239 A; 260/553 A; 7l/95;7l/120 [51] Int. Cl. C07D 295/20 R [58] Field of Search 260/326.25

[56] References cued wherein X can be oxygen or sulfur, R can be lower UNITED STATES PATENTS alkyl or two R groups can form a ring structure, R, 3,639,608 2/ I972 Adams et al Zoo/326.4 X can be hydrogen, halogen, haloalkyl, alkyl or alkoxy.

5 Claims, No Drawings I-IERBICIDAL COMPOSITIONS This is a continuation-in-part of Ser. No. 247,670, filed Apr. 26, 1972, now abandoned, which is a division of Ser. No. 99,658, filed Dec. 18, 1970, now abandoned.

DESCRIPTION OF THE INVENTION This invention is directed to a novel group of compounds which may be generally described as dialkylaminomethylene urea derivatives which are highly active herbicides. The compounds of the present invention are represented by the generic formula:

EXAMPLE 1 v Preparation of l 1-( dimethylaminomethylene 1 3 -trifluoromethylphenyl )-3 ,3-dimethylurea.

EXAMPLE 2 Preparation of l-(diethylaminomethylene)-1-(4-chlorophenyl)-3,3- diethylurea.

To 7.0 g. (0.044 moles) N,N,N,N-tetraethyldiaminomethane in ml. ethyl ether were added slowly 6.8 g. (0.044 moles) 4-chlorophenyl isocyanate dissolved in 15 ml. ether. The reagents were stirred for 18 hours at room temperature and then the solvent was evaporated to give 13.5 g. of liquid product.

Other compounds were prepared in an analogous manner starting with the appropriate starting materials as outlined above. The following is a table of compounds representative of those embodied by the present invention. Compound numbers have been assigned to them and are used for identification throughout the balance of the specification.

TABLEI Compound No. X R R 1 0 CH, H 2 C CH, 4-C1 3 0 CH, 4F

9 0 -CH,-, 3 CF, 10 o CH-,'-, 3-Cl 1 1,1 0 -CH. 4-Cl 12 0 CH, 3-Cl 13 0 CH1, 4-Br 14 0 CH, 2-F

15 0 CH, 2 CH, 15 0 CH, 4OCH,. 17 s CH, H

18 s CH, 4-1 .19 o CH,CH, H

20 s CH,CH, H

21 o CH,CH, 5 CF, 22 o CH,CH, 4-Cl 23 0 CH, 3.5-Cl 24 o CH,CH, 3.5-Cl

HERBICIDAL SCREENING TESTS As previously mentioned, the novel Compounds herein described are phytotoxic compounds which are useful and valuable in controlling various plant species. Compounds of this invention are tested as herbicides in theifollowing. manner.

Pre-emergence herbicide test. the day preceding treatment, seeds of seven different weed species are planted in individual rows using one species per row across the width of the flat. The seeds used are hairy crabgrass (Digitaria sanguinalis' (1.) Scop.), yellow foxtail (Setaria glauca (L.) Beauv.), watergrass (Echinochloa crusgalli (L.) Beauv.), California red oat (Avena sativa (L.)), redroot pigweed (Amaranthus retroflexus (L.), Indian mustard (Brassica juncea (L.) Coss.) and curly dock (Rumex Crispus (L.). Ample seeds are planted to give about 20 to 50 seedlings per row, after emergence, depending on the size of the plants. The flats are watered after planting. The spraying solution is prepared by dissolving 50 mg. of the test compound in 3 ml. of a solvent, such as acetone, containing 1% Tween 20 (polyoxyethylene sorbitan monolaurate). The following day each flat is sprayed at the rate of 20 pounds of the candidate compound per gallons of solution per acre. An atomizer is used to spray the solution on soil surface. The flats are placed in a greenhouse at 80F. and watered regularly. Two weeks later, the degree of weed control is determined by comparing the amount of germination and growth of each weed in the treated flats with weeds in several untreated control flats. The rating system is as follows:

no significant injury (0-15 percentcontrol) slight injury (25-35 percent control) -continued H- moderate injury (55-65 percent control) -H-+= severe injury or death (85400 percent control) An activity index is used to represent the total activity on all seven weed species. It is the sum of the number of plus marks, so that an activity index of 21 represents complete control of all seven weeds. The results of this test are reported in Table ll.

Post-emergence herbicide test. Seeds of five weed species including hairy crabgrass, watergrass, wild oats, lndian mustard, and curly dock and one crop pinto beans (Phaseolus vulgaris), are planted in flats as described above for pre-emergence screening. The flats are placed in the greenhouse at 72-85F. and watered daily with a sprinkler. About to 14 days after planting when the primary leaves of the bean plant are almost fully expanded and the first trifoliate leaves are just starting to form, the plants are sprayed. The spray is prepared by weighing out 50 mg. of the test compound, dissolving it in 5 ml. of acetone containing 1 percent Tween 20" (polyoxyethylene sorbitan monolaurate) and then adding 5 ml. of water. The solution is sprayed on the foliage using an atomizer. The spray concentration is 0.5% and therate would be approximately 20 lb./acre if all of the spray were retained on the plant and the soil, but some spray is lost so it is estimated that the application rate is approximately l2.5 lb./acre.

Beans are used to detect defoliants and plant growth regulators. The beans are trimmed to two or three plants per flat by'cutting off the excess weaker plants several days before treatment. The treated plants are placed back in the greenhouse and care is taken to avoid sprinkling the treated foliage with water for three days after treatment. Water is applied to the soil by means of a slow stream from a watering hose taking care not to wet the foliage. I

TABLE ll SCREENING RESULTS Compound No. Pre-emergence Post-emergence 1 21 18 2 21 18 3 21 I8 4 21 18 s 21 18 6 21 18 7 3 11 8 19 18 9 18 I6 10 18 17 a 11 18 17 12 19 I8 13 19 18 14 18 17 15 20 18 i6 14 18 17 17 I6 18 19 17 19 20 18 20 13 12 21 20 I8 22 20 18 23 19 17 24 '13 14 What is claimed 15: l. A compound of the formula:

CH -CH I1 CH CH N-CH NCN I CH2-CH cu -CH wherein R is selected from 3,5-Cl, 3-CF 3-Cl and 4-Cl.

2. The compound as set forth in claim 1 wherein R is 3,5-Cl. 7

3. The compound as set forth in claim 1 wherein R is 3-CF 4. The compound as set forth in claim 1 wherein R is 3-Cl.

5. The compound as set forth in claim 1 wherein R is 4-Cl. 

1. A COMPOUN OF THE FORMULA:
 2. The compound as set forth in claim 1 wherein R1 is 3,5-Cl.
 3. The compound as set forth in claim 1 wherein R1 is 3-CF-3.
 4. The compound as set forth in claim 1 wherein R1 is 3-Cl.
 5. The compound as set forth in claim 1 wherein R1 is 4-Cl. 